Diethyl Ether → 1-Phenylnaphthalen-2-ol

HRID 387491Notes

Reaction equation

HRID 387491 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.B(Br)(Br)Br.C(OCC)C>C(Cl)Cl>[C:13]1([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:11]=[CH:12][C:3]=2[OH:2])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 25134Boron tribromideHCID 113222662-Methoxy-1-phenylnaphthalene

Product 1

HCID 112182821-Phenylnaphthalen-2-olYield 81.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To solution of 2-methoxy-1-phenylnaphthalene (13.0 g, 55.5 mmol) in methylene chloride (300 mL), added dropwise was solution of boron tribromide (670 mL) (1M in methylene chloride) at −78° C., and the mixture reacted for three hours while slowly raising the temperature to ambient temperature. Then, mixture of ice (150 g) and diethyl ether (250 mL) was added thereto. The organic layer was isolated, and the aqueous layer was extracted with diethyl ether. The combined organic layer was dried over magnesium sulfate and evaporated to remove the volatile substances. Purification via silica gel column chromatography (eluent: mixture of hexane and methylene chloride) gave 1-phenylnaphthalen-2-ol (10.0 g, yield: 81.8%) as white solid.

Workup

  1. customthe mixture reacted for three hours
  2. additionwas added
  3. customThe organic layer was isolated
  4. extractionthe aqueous layer was extracted with diethyl ether
  5. dry with materialThe combined organic layer was dried over magnesium sulfate
  6. customevaporated
  7. customto remove the volatile substances
  8. customPurification
  9. additionvia silica gel column chromatography (eluent: mixture of hexane and methylene chloride)

Sources & evidence

ORD record
ord-f01a11eac0f54a35b3c4c4101fc7ecc4
Source dataset
uspto-grants-2013_02
Patent number
US08372996B2

Reaction notes

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